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US2130525A - Hydroxy alkyl ethers of hydrogenated hydroxy diphenyl compounds - Google Patents

Hydroxy alkyl ethers of hydrogenated hydroxy diphenyl compounds Download PDF

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US2130525A
US2130525A US126808A US12680837A US2130525A US 2130525 A US2130525 A US 2130525A US 126808 A US126808 A US 126808A US 12680837 A US12680837 A US 12680837A US 2130525 A US2130525 A US 2130525A
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hydroxy
cyclohexyl
phenol
beta
ether
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Gerald H Coleman
John W Zemba
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Dow Chemical Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • This invention concerns the hydroxy-alkyl ethers of hydrogenated hydroxy-diphenyl compounds, e. g. compounds obtained by the catalytic hydrogenation of the phenyl phenols, and nuclear substituted derivatives thereof. These compounds have the following formula:
  • RO-(C11.H2n)--OH wherein R represents an hydrogenated hydroxyldiphenyl residue, and n is an integer greater than 1.
  • R represents an hydrogenated hydroxyldiphenyl residue
  • n is an integer greater than 1.
  • cyclohexyl phenols includes the cyclohexyl phenols, the phenyl cyclohexanols, the cyclohexyl cyclohexanols, and derivatives thereof containing unreactive substituents such as chlorine, bromine,
  • These new compounds may be prepared by reacting an hydrogenated hydroxy-diphenyl compound with a mono-halo-aliphatic alcohol, e. g. a halohydrin, etc., in the presence of a suitable alkali such as sodium hydroxide, potassium hydroxide, etc.
  • a mono-halo-aliphatic alcohol e. g. a halohydrin, etc.
  • a suitable alkali such as sodium hydroxide, potassium hydroxide, etc.
  • the hydrogenated hydroxy-diphenyl compound is generally dissolved in aqueous alkali and the halo-alcohol added thereto at a reaction temperature with stirring.
  • the reaction may also be carried out by first mixing the hydrogenated derivative with the halo-alcohol and subsequently adding the alkali thereto. Good yields of the desired products can be obtained when equimolecular proportions of reactants are used.
  • the reaction may be conveniently carried out at the refluxing temperature of the mixture, but lower or higher temperatures may be employed.
  • alcohol ,or other water-miscible organic solvent may be added to the reaction mixture.
  • the mixture is allowed to stand and separate into layers, the oily layer being subsequently separated, and the desired compound isolated therefrom, as by fractional distillation under reduced no pressure.
  • Our new compounds may also be prepared by reacting an hydrogenated hydroxy-diphenyl compound with an alkylene oxide in the presence of a suitable catalyst, e. g. sulfuric acid.
  • a suitable catalyst e. g. sulfuric acid.
  • alkylene oxide e. g. butylene oxide, etc.
  • the mixture is stirred until the 5 reaction is substantially complete and thereafter washed successively with aqueous alkali and water, and fractionally distilled to obtain the desired hydroxy-alkyl ether product.
  • Example 1 A mixture of 5 mols of 2-cyclohexyl phenol, 5 mols of sodium hydroxide, and 1 liter of per cent aqueous ethanol was warmed to 70 C. with stirring, and 5 mols of ethylene chlorohydrin as a 42 per cent aqueous azeotrope slowly added there- 20 to over a period of 2 hours and at a temperature of 65 C. The reaction mixture was agitated for an additional 2 hours, diluted with 1 liter of water, and allowed to stand until Stratification occurred.
  • Example 2 In a similar manner 1 mol. each of 2-cyclohexyl-l-chloro-phenol, sodium hydroxide, and 0 ethylene chlorohydrin were reacted together in 350 milliliters of water at a temperature of (2., whereby the beta-hydroxy-ethyl ether of 2-cyclo-hexyl-4chloro-phenol was obtained as a 40 colorless oil boiling at 166 to 168 C. at 4 millimeters pressure.
  • Example 3 2 mols of ethylene oxide was passed into a mixture of 2 mols of 2-cyclohexyl-cyclohexanol 45 (boiling point -153 C. at 10 millimeters .pressure) 2 milliliters of concentrated sulphuric cessively washed with 10 per cent aqueous sodium hydroxide solution and with water and fraction- 56 ally distilled to obtain the beta-hydroxy-ethyl ether of 2-cyclohexyl-cyclohexanol as a colorless liquid boiling at 135-137 C. at 4 millimeters pressure, and having the specific gravity 1.020 at 20/4 C.
  • Example 4 Exam le 5 1 mol. of 4-cyclohexyl phenol was mixed with 1 mol. of sodium hydroxide and 250 milliliters of water, and 1 mol. of propylene chloro-hydrin as a 51 per cent azeotrope reacted therewith over a period of 1 hour and at a temperature of approximately 55 C. The reaction mixture was thereafter stirred at 65 C. for 2 hours, cooled, and the oily layer thereof fractionally distilled under reduced pressure, 150 grams of the desired ether product being thereby obtained.
  • the hydroxy-propylether of 4-cyclohexy1 phenol is a" white crystalline solid melting at 75-76 C. upon recrystallization from ligroin.
  • Example 6 2 mols of 2-cyclohexyl phenol, 2 mols of isobutylene oxide, and 2 grams of concentrated sulphuric acid were reacted together in 400 milliliters of carbon tetrachloride substantially as described in Example 3. The reaction mixture was fractionally distilled, whereby there was obtained the hydroxy-butyl ether of 2-cyclohexyl phenol as a colorless liquid boiling at 146-148 C. at 3-4 millimeters pressure, and having a specific gravity of 1.024 at 20/4 C.
  • Beta-hydroxy-ethyl ether of -cyclohexyl phenol a white crystalline solid boiling between 169 and 173 C. at 4'millimeters pressure, and having a melting point of 62-63 C.;
  • beta-hydroxy-ethyl ether 01. 2-cyclohexyl-4- bromo-phenol; beta-hydroxy-ethyl ether of 2- cyclohexyl-E-bromo-phenol; beta-hydroxy-ethyl ether of 2 cyclohexyl-6-bromo-phenol; beta-hydroxy-ethyl ether of 2-(2-bromo-cyclohexyhphenol; beta-hydroxy-ethyl ether of 2-(3-bromocyclohexyl)-phenol; beta-hydroxy-ethyl ether of 2- (4-bromo-cyclohexyl) -phenol; beta-hydroxyethyl ether of 2,4-dichloro-6-cyclohexyl phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl- 3,6-dichloro-phenol; beta-hydroxy-ethyl ether of 2-(4- chloro-cyclohexyl) -4-chloro-
  • the beta-hydroxy-ethyl ether of 4-cyclohexyl phenol in 5 per cent kerosene solution killed 19.3 per cent of the files contacted therewith.
  • n is an integer from 2 to 4, inclusive, and R represents an hydrogenated hydroxy-diof 4-cyclohexyl phenol; hydroxy-butyl formula:
  • I 3 phenyl residue selected from the class consisting of the cyclohexyl-phenyl, phenyl-cyclohexyl, and cyclohexyl-cyclohexyl radicals and analogues thereof containing substituents non-reactive with acids and alkalies in the etherification reaction.
  • R. represents an hydrogenated hydroxydiphenyl residue selected from the class consisting of the cyclohexyl phenyl, phenyl-cyclohexyl, and cyclohexyl-cyclohexyl radicals and analogues thereof containing substituents non-reactive with acids and alkalies in the etheriflcation reaction.
  • n is an integer from 2 to 4, inclusive.
  • n is an integer from 2 to 4, inclusive.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented Sept. 20, 1938 HYDROXY ALKYL ETHERS OF- HYDROGEN- ATED HYDROXY DIPHENYL COMPOUNDS Gerald H. Coleman and John W. Zemba, Midland, Mich., assignors to The Dow Chemical Company, Midland, Michigan Mich., a corporation of No Drawing. Application February 20, 1937, Serial No. 126,808
' lZ Claims. (Cl. 260-150) This invention concerns the hydroxy-alkyl ethers of hydrogenated hydroxy-diphenyl compounds, e. g. compounds obtained by the catalytic hydrogenation of the phenyl phenols, and nuclear substituted derivatives thereof. These compounds have the following formula:
RO-(C11.H2n)--OH wherein R represents an hydrogenated hydroxyldiphenyl residue, and n is an integer greater than 1. The term hydrogenated hydroxy-diphenyl,
as herein employed, includes the cyclohexyl phenols, the phenyl cyclohexanols, the cyclohexyl cyclohexanols, and derivatives thereof containing unreactive substituents such as chlorine, bromine,
15 alkyl, and aryl radicals, etc., attached to one or both of the S-membered carbon rings.
We have prepared members of this class of compounds, determined certain physical characteristics thereof whereby they may be readily identified, and found that they are particularly useful in the preparation of compositions for the control of house-hold insect pests.
These new compounds may be prepared by reacting an hydrogenated hydroxy-diphenyl compound with a mono-halo-aliphatic alcohol, e. g. a halohydrin, etc., in the presence of a suitable alkali such as sodium hydroxide, potassium hydroxide, etc.
In preparing our new compounds, the hydrogenated hydroxy-diphenyl compound is generally dissolved in aqueous alkali and the halo-alcohol added thereto at a reaction temperature with stirring. The reaction may also be carried out by first mixing the hydrogenated derivative with the halo-alcohol and subsequently adding the alkali thereto. Good yields of the desired products can be obtained when equimolecular proportions of reactants are used. The reaction may be conveniently carried out at the refluxing temperature of the mixture, but lower or higher temperatures may be employed. In certain cases, where the reactants are not appreciably soluble in aqueous alkali, alcohol ,or other water-miscible organic solvent may be added to the reaction mixture. Following completion of the reaction, the mixture is allowed to stand and separate into layers, the oily layer being subsequently separated, and the desired compound isolated therefrom, as by fractional distillation under reduced no pressure.
Our new compounds may also be prepared by reacting an hydrogenated hydroxy-diphenyl compound with an alkylene oxide in the presence of a suitable catalyst, e. g. sulfuric acid. The
56 alkylene oxide, e. g. butylene oxide, etc., can be passed into a mixture of the hydrogenated hydroxy-diphenyl compound, catalyst, and an inert organic solvent, e. g. carbon tetrachloride, at temperatures below the boiling point of the reaction mixture. The mixture is stirred until the 5 reaction is substantially complete and thereafter washed successively with aqueous alkali and water, and fractionally distilled to obtain the desired hydroxy-alkyl ether product.
The following examples describe thepreparation 10 of certain representative members of our new group of compounds, but are not to be construed as limiting the invention:
Example 1 A mixture of 5 mols of 2-cyclohexyl phenol, 5 mols of sodium hydroxide, and 1 liter of per cent aqueous ethanol was warmed to 70 C. with stirring, and 5 mols of ethylene chlorohydrin as a 42 per cent aqueous azeotrope slowly added there- 20 to over a period of 2 hours and at a temperature of 65 C. The reaction mixture was agitated for an additional 2 hours, diluted with 1 liter of water, and allowed to stand until Stratification occurred. The oily layer was then separated and 25 fractionally distilled whereby 4.04 mols of the beta-hydroxy-ethyl ether of 2-cyclohexyl phenol was obtained as a viscous liquid boiling at 161- 163 C. at 4 millimeters pressure and having a specific gravity of 1.061 at 20/4 C. This com- 30 pound was substantially insoluble in water but somewhat soluble in most organic solvents.
Example 2 In a similar manner 1 mol. each of 2-cyclohexyl-l-chloro-phenol, sodium hydroxide, and 0 ethylene chlorohydrin were reacted together in 350 milliliters of water at a temperature of (2., whereby the beta-hydroxy-ethyl ether of 2-cyclo-hexyl-4chloro-phenol was obtained as a 40 colorless oil boiling at 166 to 168 C. at 4 millimeters pressure.
Example 3 2 mols of ethylene oxide was passed into a mixture of 2 mols of 2-cyclohexyl-cyclohexanol 45 (boiling point -153 C. at 10 millimeters .pressure) 2 milliliters of concentrated sulphuric cessively washed with 10 per cent aqueous sodium hydroxide solution and with water and fraction- 56 ally distilled to obtain the beta-hydroxy-ethyl ether of 2-cyclohexyl-cyclohexanol as a colorless liquid boiling at 135-137 C. at 4 millimeters pressure, and having the specific gravity 1.020 at 20/4 C.
Example 4 Exam le 5 1 mol. of 4-cyclohexyl phenol was mixed with 1 mol. of sodium hydroxide and 250 milliliters of water, and 1 mol. of propylene chloro-hydrin as a 51 per cent azeotrope reacted therewith over a period of 1 hour and at a temperature of approximately 55 C. The reaction mixture was thereafter stirred at 65 C. for 2 hours, cooled, and the oily layer thereof fractionally distilled under reduced pressure, 150 grams of the desired ether product being thereby obtained. The hydroxy-propylether of 4-cyclohexy1 phenol is a" white crystalline solid melting at 75-76 C. upon recrystallization from ligroin.
Example 6 2 mols of 2-cyclohexyl phenol, 2 mols of isobutylene oxide, and 2 grams of concentrated sulphuric acid were reacted together in 400 milliliters of carbon tetrachloride substantially as described in Example 3. The reaction mixture was fractionally distilled, whereby there was obtained the hydroxy-butyl ether of 2-cyclohexyl phenol as a colorless liquid boiling at 146-148 C. at 3-4 millimeters pressure, and having a specific gravity of 1.024 at 20/4 C.
Other compounds prepared in a similar manner include the following:
Beta-hydroxy-ethyl ether of -cyclohexyl phenol,a white crystalline solid boiling between 169 and 173 C. at 4'millimeters pressure, and having a melting point of 62-63 C.;
Hydroxy-propyl ether of 2-cyclohexyl phenol, a colorless liquid boiling at 147149 C. at 3 millimeters pressure and having a specific gravity of 1.0289 at 20/4 C.
Other hydrogenated hydroxydiphenyl compounds, halo-alcohols, and alkylene oxides may be substituted for those shown in the examples to obtain a large number of hydroxy-alkyl ether compounds falling within the scope of this invention, e, g. beta-hydroxy-ethyl ether of 3- cyclohexyl phenol; beta-hydroxy-ethyl ether of 3-phenyl-cyclohexano1 beta-hydroxy-ethyl ether of 4-phenyl-cyclohexanol; beta-hydroxy-ethyl .ether of 3-cyclohexyl-cyclohexanol; beta-hydroxy-ethyl ether of i-cyclohexyl-oyclohexanol; beta-hydroxy-ethyl ether of 2-cyclohexyl-3-chloro-phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl-5-chloro-phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl-6-chloro-phenol; beta-hydroxyethyl ether of 2-(2-chloro-cyclohexyl)phenol; beta-hydroxy-ethyl ether of 2-(3-chloro-cyc1ohexyD-phenol; beta-hydroxy-ethyl ether of 2- (4 chloro cyclohexyl) phenol; beta-hydroxyethyl ether of 2-cyclohexyl-3-bromo-phenol;
beta-hydroxy-ethyl ether 01. 2-cyclohexyl-4- bromo-phenol; beta-hydroxy-ethyl ether of 2- cyclohexyl-E-bromo-phenol; beta-hydroxy-ethyl ether of 2 cyclohexyl-6-bromo-phenol; beta-hydroxy-ethyl ether of 2-(2-bromo-cyclohexyhphenol; beta-hydroxy-ethyl ether of 2-(3-bromocyclohexyl)-phenol; beta-hydroxy-ethyl ether of 2- (4-bromo-cyclohexyl) -phenol; beta-hydroxyethyl ether of 2,4-dichloro-6-cyclohexyl phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl- 3,6-dichloro-phenol; beta-hydroxy-ethyl ether of 2-(4- chloro-cyclohexyl) -4-chloro-phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl-4,6-dibromophenol; beta-hydroxy-ethyl ether of 2%(3-chlorocyclohexyl) -'-4-bromo-phenol; beta-hydroxy-ethyl ether of 3-cyclohexyl-4-chloro-phenol; betahydroxy-ethyl ether of 3-cyclohexyl-6-chlorophenol; beta-hydroxy-ethyl ether of 3-cyclohexyl-4-bromo-phenol; beta-hydroxy-ethyl ether of 3-cyclohexyl-G-bromo-phenol; beta-hydroxyethyl ether of 3-cyclohexyl-4-bromo-6-chlorophenol; beta-hydroxy-ethyl ether of 3-(4-chlorocyclohexyDphenol; beta-hydroxy-ethyl ether of 3- (2-chloro-cyclohexyl) -4-bromo-phenol; betahydroxy-ethyl ether of 2-chloro-4-cyclohexyl phenol; beta-hydroxy-ethyl ether of 2,6-dichloro- 4-cyclohexyl phenol; beta-hydroxy-ethyl ether of 3-chloro-4-cyclohexyl phenol; beta-hydroxy-ethyl ether of 2-bromo-4-cyclohexyl phenol; beta-hydroxy-ethyl ether of 2,6-dibromo-4-cyclohexyl phenol;beta-hydroxy-ethyl ether of 2-bromo-4- cyclohexyl-fi-chloro-phenol; beta-hydroxy-ethyl ether of 4-(4-bromo-cyclohexyl)-phenol; betahydro'xy-ethyl ether of 4-(2-chloro-cyclohexyl)- phenol; beta-hydroxy-ethyl ether of 4-(2-chlorocyclohexyl) -6-chloro-phenol beta-hydroxy-ethyl ether of 2-cyclohexyl-4-methyl phenol; beta-hydroxy-ethyl ether of 2-methyl-4-cyclohexyl phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl- 4-tertiary-butyl phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl-4-tertiary-biityl-6-chlorophenol; beta-hydroxy-ethyl ether of 2-cyclohexyl-4-benzy1 phenol; beta-hydroxy-ethyl ether of 2-(3-methyl-cyclohexyl)-phenol; beta-hydroxy-ethyl ether of 4-(1-methyl-cyclohexyi')- phenol; beta-hydrox-y-ethyl ether of 4-(1-phenylcyclohexyl)-phenol; beta-hydroxy-ethyl ether of 2-cyclohexyl-6-methoxy-phenol; beta-hydroxyethyl ether of 2-ethoxy-4-cyclohexyl phenol; beta-hydroxy-ethyl ether of 2-phenyl-4-chlorocyclohexanol; beta-hydroxy-ethyl ether of 4- pheny1-6-methyl-cyclohexanol; beta-hydroxyethyl ether of 4-(4-bromo-phenyl)-2-metliylcyclohexanol; beta-hydroxy-ethyl ether of 4-(4- bromo-phenyl) -2-chloro-cyclohexanol; beta-hydroxy-ethyl ether of 4-cyclohexyl-fi-chloro-cyclohexanol; beta-hydroxy-ethyl ether of Z-cyclohexyl-4-tertiary-butyl-cyclohexanol; beta-hydroxy-ethyl ether of 2-(3-methyl-cyclohexyD- cyclohexanol; beta-hydroxy-ethyl ether of 4-(1- phenyl-cyclohexyl) -cyclohexanol hydroxy-pro- 'pyl ether of 3-cyclohexyl phenol; hydroxy-propyl ether of Z-phenyl-cyclohexanol; hydroxy-propyl ether of 4-cyclohexyl-cyclohexanol; hydroxy-propyl ether of 2-cyclohexyl-4-cliloro-phenol; hydroxy-propyl ether of 2-cyclohexyl-6-chloro-phenol; hydroxy-propyl ether of 2,4-dichloro-6- cyclohexyl phenol; hydroxy-propyl ether of 2- cyclohexyl-4bromophenol; hydroxy-propyl ether of 2cyclohexyl6-bromo-phenol; hydroxypropyl ether of 2-cyclohexyl4,6-dibromo-phenol; hydroxy-propyl ether of 3-cyclohexyl-4- chloro-phenol; hydroxy-propyl ether of 3-cyclohexyl-4,6-dibromo-phenol; hydroxy-propyl ether of 2-chloro-4-cyclohexyl phenol; hydroxy-propyl ether of 2,6-dichloro-4-cyclohexyl phenol; hydroxy-propyl ether of 2-bromo-4-cycohexyl phenol; hydroxy-propyl ether of 2,6-dibromo-4- cyclohexyl phenol; hydroxy-propyl ether of 2- methyl-4-cyclohexyl phenol; hydroxy-propyl ether of 2-(3 -methyl-cyclohexyl)phenol; hydroxy-propyl ether of 4-(1-methyl-cyclohexyD- phenol; hydroxy-propyl ether of 4'-(1-phenylcyclohexyD-phenol; hydroxy-propyl ether of 2- methoxy-4-cyclohexyl phenol; hydroxy-butyl ether of 3-cyclohexyl phenol; hydroxy-butyl ether ether ether of 2-phenyl-cyclohexanol; hydroxy-butyl of 4-phenyl-cyclohexanol; hydroxy-butyl ether of 2-cyclohexyl-cyclohexanol; hydroxybutyl ether of 4-cyclohexyl-cyclohexanol; hydroxv-butyl ether of 2-cyclohexyl-4chloro-phenol; hydroxy-butyl ether of 2-cyclohexyl-4,6-dichloro-phenol; hydroxy-butyl ether of 2,6-dichloro--cyclohexyl phenol; hydroxy-butyl ether of 2,6-dibromo-4-cyclohexyl phenol; hydroxypentyl ether of 2-cyclohexyl phenol; hydroxypentyl ether of 4-cyclohexyl phenol; hydroxypentyl ether of 2-phenyl-cyclohexanol; hydroxypentyl ether of 2-cyclohexyl-cyclohexanol; hydroxy-pentyl ether of 2-cyclohexyl 4-chloro-phenol; hydroxy-pentyl ether of 2-chloro-4-cyclohexyl phenol; hydroxy-pentyl ether of 2,6-dichloro-4-cyclohexyl phenol; etc.
Representative members of the above-described group of compounds have been tested by the Feet-Grady method as described in Soap, 8, No. 4, 1932, and found to be particularly useful as fly spray toxics. For example, a 5 per cent solution of the beta-hydroxy-ethyl ether of 2-cyclohexyl phenol in kerosene, when tested'against 3 day old house flies, showed a 7'7 per cent knockdown and a kill of 32.4 per cent after 24 hours.
The beta-hydroxy-ethyl ether of 4-cyclohexyl phenol in 5 per cent kerosene solution killed 19.3 per cent of the files contacted therewith.
Other modes of applying the principle of our invention may be employed instead of those explained, change being made as regards the materials employed provided theproducts described in the following claims be thereby obtained.
We, therefore, particularly point out and distinctly claim as our invention:
1. A compound having the formula:
wherein n is an integer from 2 to 4, inclusive, and R represents an hydrogenated hydroxy-diof 4-cyclohexyl phenol; hydroxy-butyl formula:
. I 3 phenyl residue selected from the class consisting of the cyclohexyl-phenyl, phenyl-cyclohexyl, and cyclohexyl-cyclohexyl radicals and analogues thereof containing substituents non-reactive with acids and alkalies in the etherification reaction.
3. A beta-hydroxy-ethyl ether of an hydrogenated hydroxy-diphenyl compound having the formula:
RO--CH2CH:OH
wherein R. represents an hydrogenated hydroxydiphenyl residue selected from the class consisting of the cyclohexyl phenyl, phenyl-cyclohexyl, and cyclohexyl-cyclohexyl radicals and analogues thereof containing substituents non-reactive with acids and alkalies in the etheriflcation reaction.
4. An hydroxy-propyl ether of an hydrogenated hydroxy-diphenyl compound having the cur-on, ofi, lingocanyon car-on, wherein n is an integer greater than 1.
6. An hydroxy-alkyl ether of a cyclohexyl' phenol having the formula:
/OH CH| 0H. ERGO-(matron march,
wherein n is an integer from 2 to 4, inclusive.
7. The beta-hydroxy-ethyl ether of cyclohexyl phenol.
8. An hydroxy-propyl ether of cyclohexyl phenol.
9. An hydroxy-butyl ether of cyclohexyl phenol.
10. An hydroxy-alkyl ether of z-cyclohexyl phenol having the formula:
wherein n is an integer from 2 to 4, inclusive.
11. Beta-hydron-ethyl ether of 2-cyclohexyl phenol.
12. Hydroxy-propyl ether of 2-cyclohexyl phenol, a colorless liquid boiling between 147 and 149 C. at 3 millimeters pressure, and having a specific gravity of 1.0289 at 20l4 C.
. GERALD H. COLEMAN.
JOHN W. MA.
US126808A 1937-02-20 1937-02-20 Hydroxy alkyl ethers of hydrogenated hydroxy diphenyl compounds Expired - Lifetime US2130525A (en)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2440093A (en) * 1943-07-12 1948-04-20 Ind Rayon Corp Terpene derivatives and method of producing the same
US2453634A (en) * 1944-05-27 1948-11-09 Shell Dev Glycidyl ethers
US2558513A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2558511A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2558512A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2558510A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2567350A (en) * 1946-08-05 1951-09-11 Parke Davis & Co Omega-haloalkyl benzhydryl ether and methods of making same
US2572885A (en) * 1949-09-28 1951-10-30 Petrolite Corp Certain polyol ethers
US2572886A (en) * 1949-09-28 1951-10-30 Petrolite Corp Certain polyol ethers
US2574542A (en) * 1949-11-01 1951-11-13 Petrolite Corp Certain para-cyclohexylcyclohexanol ethers of certain glycols
US2574541A (en) * 1949-11-01 1951-11-13 Petrolite Corp Certain para-cyclohexylcyclohexanol ethers of certain glycols
US5395766A (en) * 1991-01-11 1995-03-07 Chisso Corporation Optically active trans-2-aryl-1-cyclohexanol derivatives and a process for producing the compounds

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2440093A (en) * 1943-07-12 1948-04-20 Ind Rayon Corp Terpene derivatives and method of producing the same
US2453634A (en) * 1944-05-27 1948-11-09 Shell Dev Glycidyl ethers
US2567350A (en) * 1946-08-05 1951-09-11 Parke Davis & Co Omega-haloalkyl benzhydryl ether and methods of making same
US2572885A (en) * 1949-09-28 1951-10-30 Petrolite Corp Certain polyol ethers
US2572886A (en) * 1949-09-28 1951-10-30 Petrolite Corp Certain polyol ethers
US2558513A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2558511A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2558512A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2558510A (en) * 1949-11-01 1951-06-26 Petrolite Corp Processes for breaking petroleum emulsions
US2574542A (en) * 1949-11-01 1951-11-13 Petrolite Corp Certain para-cyclohexylcyclohexanol ethers of certain glycols
US2574541A (en) * 1949-11-01 1951-11-13 Petrolite Corp Certain para-cyclohexylcyclohexanol ethers of certain glycols
US5395766A (en) * 1991-01-11 1995-03-07 Chisso Corporation Optically active trans-2-aryl-1-cyclohexanol derivatives and a process for producing the compounds

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